
Sennheiser
HD 560S
Budget gaming king with clear sound, but tight fit.

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Mine was the Logitech G432, but my sisters decided to be assholes and break it :( https://preview.redd.it/143lmhjuj7xg1.jpeg?width=3060&format=pjpg&auto=webp&s=b2e4c61463e9cf40dbc1735bdc4c97e0274c8d49
So ON ear headphones press on the shell of the ear. OVER ear headphones rest against the skull around the ear. If you get a large-cupped over ear model, it will only interact with your glasses by pressing the frame right in front of the ear - but that spot can be less sensitive than the shell of the ear getting sandwiched. I see the headphones you mention, the logitech g432, they should be over ear BUT the inner space of the ear cup looks small - might be too small for your ears. Also if your skull is larger you want to have a bit less clamp force. I wear some corsair virtuoso - they are wireless convertible, and the ear cups are fully round. So I can put them on and shift them about until the rounded back edge is just behind the shell of my ear. Also the ear cups swivel nicely, and I twist them a bit so they are tighter behind the ear and looser at the front, where they touch my glasses arm.
Unless you have dumbo ears the pads on the G432 shouldn’t be touching your ear at all. They are over ear headphones which means the pads are designed to rest directly against your head. If your ears are pinched between the pad and your head then you’re wearing the headphones wrong.
Yeah, I uhhh... I'm not sure it's entirely having the tiny ears thing here. Is this for headphones to wear to school? We struggle with this every year. My kid who is sensitive to a lot of different things really has an affinity for goofy gamer headsets now. He wears a Logitech G432 to school now, and it feels goofy and overkill, but it's the only headphone he's had at school that didn't result in a bunch of meltdowns. You can find a used set on eBay for less than $10. We got his from there and I needed to replace the earpads, but those were only a few bucks. At home he wears the HyperX Cloud Stinger 2 Cores, which are like $30. For Xmas I got him Koss GMR-54X's. He didn't like them at first, but really came around to them. Got them from Drop, who is out of stock right now, but they get them back in intermittently. Also, I can't help but think it sounds like your kiddo has sensory issues and maybe you're struggling with it. It's okay. Lots of kids do, but it might be a symptom of other stuff kicking around in their head. Most kids just wear headphones and don't complain.
I just leaned into good build quality/comfort/low cost and grabbed a Logitech G432 on sale and have been perfectly happy with it since I got my Series X. It's not flashy and is missing some features you might prefer, but it serves its purpose quite well for me. I did a lot of work for years with someone who would always splurge for really expensive headsets and I couldn't tell you how many times I'd have to return them because one thing or another would always go wrong. They'd spend many hundreds of dollars on gaming headsets and go through them on a semi-annual basis.
https://preview.redd.it/h17z2kz686wg1.png?width=959&format=png&auto=webp&s=f9591366dccd3edde01966cd867a6e2c6b2ba9b1 I've had these glasses since 2021, the headphones (HE400SE, the cables are removed, don't ask about the headband) since 2022, honestly never felt them to be annoying. Glasses frame arm between my earlobe and my head, and a softly padded, large over-ear headphones surrounding my earlobe is.. comfy. >my glasses sit on my ears I'm not sure what you mean by this, but seeing the G432 reviews, I can tell they're the main culprit. Small earpad pushing *on* the earlobes, and a high clamping force. I never liked on-ear headphones because of that. Though you *might* just be able to reduce the clamping force, some models of headphones can be adapted by leaving them clamping a stack of books overnights when you're not using them, for a couple of weeks, the clamping force will be reduced. Sennheiser HD600 are known for this.

Sennheiser
HD 560S
Budget gaming king with clear sound, but tight fit.

Sony
WH-1000XM4
ANC king, durable, but unreliable mic and touch controls.

Sennheiser
HD 6XX
Legendary mids, durable, but narrow soundstage and weak bass.

Sennheiser
HD 490 PRO
Super comfortable, wide soundstage for gaming, versatile pads.

Sennheiser
HD 599
Super comfortable, easy to drive, wide soundstage, open-back.

Ranked #1
Sennheiser - HD 6XX

Ranked #1
FiiO - FT1 Closed-back Headphones

Ranked #1
Sennheiser - HD 560S

Ranked #1
Sony - MDR-7506

Ranked #1
Sony - WH-1000XM4

Ranked #1
Sennheiser - HD 560S